Tag: M.W=100-200

2058-74-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2058-74-4 as follows.

A solution of N-methylisatin (322 mg, 2.0 mmol), indole (258 mg, 2.2 mmol), and K 2 CO 3 (138 mg, 1.0 mmol) in aqueous DMF (H 2 O/DMF, 2:1, 5.0 mL) was heated to 50 o C for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 1:1), 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one was obtained as a white solid, 340 mg (61%). A solution of 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one (278 mg, 1.0 mmol), 5-methyl-1H-indole (131 mg, 1.0 mmol), and p-TsOH . H 2 O (19 mg, 0.1 mmol) in CH 2 Cl 2 (2.0 mL) was stirred at room temperature for 1 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 2:1), 5,1′-dimethyl-1H,1’H,1”H-[3,3′;3′,3”]terindol-2′-one was obtained as a white solid, 348 mg (89%). To a stirred solution of 5,1′-dimethyl-1H,1’H,1”H-[3,3′;3′,3”]terindol-2′-one (196 mg, 0.5 mmol) in DMF (3.0 mL) was added t-BuOK (125 mg, 1.1 mmol) and iodomethane (158 mg, 1.1 mmol) successively at 0 o C. The reaction mixture was stirred at room temperature for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 3:1), compound 1g was obtained as a white solid, 156 mg (74%). Compound 1h was synthesized similarly, and the spectroscopic data of unknown compounds 1g and 1h are as follows. Compound 1g: 74%; pale yellow solid, mp 202-204 o C; IR (KBr) 1716, 1490, 1469, 1370, 1340 cm -1 ; 1 H NMR (CDCl 3 , 500 MHz) 1gNOMeNNMeMeMe6 delta 2.31 (s, 3H), 3.35 (s, 3H), 3.66 (s, 3H), 3.69 (s, 3H), 6.79 (s, 1H), 6.86 (s, 1H), 6.93 (t, J = 7.5 Hz, 1H), 6.95-7.05 (m, 3H), 7.12 (s, 1H), 7.13-7.19 (m, 2H), 7.21 (d, J = 8.1 Hz, 1H), 7.27 (d, J = 8.1 Hz, 1H), 7.33 (t, J = 7.7 Hz, 1H), 7.43 (d, J = 7.2 Hz, 1H); 13 C NMR (CDCl 3 , 125 MHz) delta 21.6, 26.6, 32.75, 32.77, 52.7, 108.0, 108.9, 109.2, 113.0, 113.7, 118.9, 121.12, 121.13, 121.4, 122.6, 123.2, 125.3, 126.3, 126.5, 127.9, 128.0, 128.8, 128.9, 134.2, 136.2, 137.7, 142.9, 177.8; MALDI-TOF m/z 420 [M+H] + .

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Seo, Da Young; Kim, Gieun; Jo, Hwi Yul; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 39; 4; (2018); p. 587 – 590;,
Indoline – Wikipedia,
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These common heterocyclic compound, 496-12-8, name is Isoindoline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 496-12-8

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1 H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSOd6) 10.45 (1 H, s), 10.32 (1H1 s), 7.36 (1 H, br.s), 7.35 (1 H, s), 7.28 (3H, br.s), 6.59 (1 H, s), 4.77 (2H, br.s), 4.71 (2H, br.s). MS: [M+H]+ 332/334.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 496-12-8.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2913-97-5, Name is N-(2-Oxoethyl)phthalimide, 2913-97-5, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

EXAMPLE 6E tert-butyl (2S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3,3-dimethylbutanoate A solution of the product of Example 3E (9.34 g, 49.4 mmol) in methanol (33 mL) was treated with L-tert-leucine tert-butyl ester hydrochloride (10 g, 44.9 mmol), sodium cyanoborohydride (5.6 g, 89.8 mmol), and acetic acid (1.5 ml, 26.2 mmol), stirred at 25¡ã C. for 4 hours, and partitioned between chloroform and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel, eluding with first with 66percent chloroform in hexanes and then with 33percent ethyl acetate in chloroform to give the title compound (10.5 g, 59percent yield).

Statistics shows that N-(2-Oxoethyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 2913-97-5.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; Yeung, Ming C.; Randolph, John T.; Wang, Xiu C.; Yu, Su; US2005/148623; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 496-12-8.

General procedure: Benzyl bromide 3 (1.0 eq), the appropriate nucleophile (1.2 eq), and K2CO3 (1.2 eq) were dissolved in dry DMF (3 mL) under an inert atmosphere. The reaction stirred at room temperature overnight.The reaction mixture was partitioned between 2 M NaOH and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate. Combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum to obtain the product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 496-12-8.

Reference:
Article; Montgomery, Deanna; Anand, Jessica P.; Baber, Mason A.; Twarozynski, Jack J.; Hartman, Joshua G.; Delong, Lennon J.; Traynor, John R.; Mosberg, Henry I.; Molecules; vol. 24; 23; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 317-20-4

Add in a 25 mL round bottom flask(E) -N-4-chlorobenzyl) -N- (4-methylbenzyl) -2-nitroethylene-1,1-diamine(1 mmol)And 7-fluoroindoline-2,3-dione (1.1 mmol), toluene (15 ml) and acetic acid (1 mlMole) was heated under magnetic stirring to 110 C for 14 hours. TLC monitoring reaction until the point of complete disappearance of raw materials, the reaction solutionThe mixture was extracted with 50 ml of ethyl acetate and 50 ml of saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfateDry, with petroleum ether / ethyl acetate = 7: 1 eluent silica gel column was dried to give a yellow solidThe product N- (4-chlorobenzyl) -2-(4-chlorobenzylamino) -7-fluoro-3-nitroquinoline-4-carboxamide (compound 30) in 75% yield.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 317-20-4.

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 84B (225 mg, 1.0 mmol), 197 isoindolin-1-one (133.1 mg, 1.0 mmol), 51 Pd2(dba)3 (28 mg, 0.03 mmol), Xantphos (29 mg, 0.05 mmol) and 50 Cs2CO3 (391 mg, 1.2 mmol) in 52 dioxane (45 mL) was heated to 100 C. overnight. After cooling to room temperature, the reaction mixture was filtered. The filtrate was concentrated under vacuum and the residue was purified by column chromatography on silica gel (1%-30% 32 EtOAc in 60 pet. ether) to provide 233 compound 84 (170 mg, 61% yield) as a white solid: 1H NMR (400 MHz, CDCl3) delta 8.72 (dd, J=7.6 Hz, 6.4 Hz, 1H), 8.57 (d, J=1.2 Hz, 1H), 8.01-7.94 (m, 3H), 7.86 (d, J=0.8 Hz, 1H), 7.69-7.65 (m, 1H), 7.59-7.52 (m, 2H), 5.14 (s, 2H) ; ESI m/z 278.0 [M+H]+ .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindolin-1-one, its application will become more common.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

20876-36-2, Adding a certain compound to certain chemical reactions, such as: 20876-36-2, name is 5-Aminoindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20876-36-2.

5-(4-Methoxycarbonylbenzamido)-2-oxindole A mixture of 82.0 mg 5-amino-2-oxindole and 131.0 mg 4-methoxycarbonylbenzoyl chloride in pyridine was stirred at room temperature for 3 hr and poured into ice water. The precipitate was filtered, washed with water and dried in a vacuum oven to give 138.0 mg of 5-(4-methoxycarbonylbenzamido)-2-oxindole (81percent yield).

According to the analysis of related databases, 20876-36-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 59-48-3

2. 5-Amino-3-(3,5-diethyl-1H-pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one 2-Oxindole (6.5 g) was dissolved in 25 mL of concentrated sulfuric acid and the mixture maintained at -10-15 C. while 2.1 mL of fuming nitric acid was added dropwise. After the addition of the nitric acid, the reaction mixture was stirred at 0 C. for 0.5 hr and poured into ice-water. The precipitate was collected by filtration, washed with water and crystallized from 50% acetic acid. The final crystalline product was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-1,3-dihydro-indol-2-one.

The chemical industry reduces the impact on the environment during synthesis Indolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sugen, Inc.; US6846839; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

324-03-8,Some common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In a RB flask charge under stirring at 2530 C, 336 gr of crude compound of formula lila (0,0203 mole) and dissolve in 336 mL tetrahydrofuran. To the clear solution add 1.902 gr cyanoacetic acid (0.0224 mole) and 2.7 mL triethylamine (0.0194 mole). Warm up reaction mass to reflux and continue stirring overnight.When reaction is completed, allow reaction mass to cool down (2530 C). Concentrate solvent till total dryness. To the oily residue add 168 mL D.M. water and extract three times with 336 mL ethyl acetate (each time). Combine organic layers, dry over sodium sulfate, filter and evaporate solvent till total dryness, to provide 4.116 gr of crude compound of formula ha,IH NMR (300 MHz, DMSOd6) 7,47 (dd, J1 = 82 Hz, J2 = 56 Hz, 1H), 689 682(m, 1H), 67 (dd, Ji = 9,2 Hz, J2 = 24 Hz, 1H), 664 (s, 1H), 336 (s, IH), 309 294(m, 2H). 13C NMR (75 MHz, DMSOd6) 177,4, 1636, 1439, 1438, 126,2, 1 17A, 1085, 987, 720, 26,4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 324-03-8, its application will become more common.

Reference:
Patent; PHARMATHEN S.A.; KOFTIS, V. Theocharis; NEOKOSMIDIS, Efstratios; RAPTIS, Christos; TRAKOSSAS, Sakellarios; ANDREOU, Thanos; VARVOGLI, Anastasia – Aikaterini; (30 pag.)WO2017/67670; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 59-48-3, name is Indolin-2-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 59-48-3

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3¡Á30 mL). The combined organic layer washed with H2O (2¡Á10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 59-48-3.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem